Raid on Cadiz

The Raid on Cadiz (29 April-1 May 1587), nicknamed "the Singeing of the King of Spain's Beard", was a raid launched by the English fleet of Sir Francis Drake against the Spanish port city of Cadiz. The English  destroyed 3 Spanish ships, with a combined tonnage of 100, and they captured 4; the raid did little damage, but it was an embarrassment of King Philip II of Spain.

On 12 April 1587, Francis Drake's English fleet set sail from Plymouth, and Queen Elizabeth I of England instructed him to not conduct hostilities against the Spanish fleet or ports a week later; Drake never received the message, as the Queen had intended for the message to serve only as plausible deniability for Drake's actions. Drake discovered that the Spanish were planning to sail a huge war fleet from Cadiz, Spain to Lisbon, Portugal, so Drake took this opportunity to raid the Spanish fleet at its harbor. At dusk on 29 April 1587, the English fleet entered the Bay of Cadiz, and the Spanish galleons were sent out to face Drake's fleet. However, the English superiority in numbers forced the Spanish ships to retreat. Spanish coastal artillery inflicted minor damage on the English fleet, but landings at El Puntal were thwarted. During the night of the 29th and all of the next day, battle raged in the bay, and the English destroyed three Spanish ships (100 tons of goods) and captured four provision-laden ships.

Drake's fleet proceeded to raid along the coast of Portugal, storming the fortresses of Sagres, Baleeira, Beliche, and Cape St. Vincent. On 8 June, the English captured the Portuguese carrack Sao Felipe off the Azores, seizing the ship after its return run from the East Indies; the English seized an enormous fortune of gold, spices, and silk. Over 100 Spanish vessels of different tonnages were destroyed in Drake's expedition, and Spanish plans for the invasion of England had to be postponed for a year due to the material and economic losses inflicted upon them.